Azoic coloring matters of fast bases of the triazine series



Patented Sept. 28, 1954 AZOIC COLORING MATTERS OF FAST BASES OF THE TRIAZINE SERIES Frederick Brody, New York, N. Y., assignor to American Cyanamid Company, New York, N. Y., a corporation of Maine N Drawing. Original application March 1, 1952,

Serial No. 274,488. Divided and this application December 29, 1953, Serial No. 401,039

4 Claims.

The present invention relates to azoic coloring matters having the following formula:

C5115 O R in which R is lower alkyl and R is a residue of an ice-color coupling component.

In the past it has been a considerable problem to obtain azoic coloring matters which have a greenish blue shade. For the most part, the few coloring matters having the desired shade have been expensive and have had other unsatisfactory characteristics. Among the compounds of the present invention those in which R. is a residue of an arylide of 2-hydroxy-3-naphthoic acid are blue azo coloring matters of a very desirable green shade which have good fastness and other properties. They constitute the preferred embodiment of the present invention, although in a broader aspect the invention is not limited thereto.

Although the intermediate amines used in preparing the diazo components of the colors of the present invention, that is to say, compounds corresponding to the above formula in which -N=NR is replaced by -NH2, are themselves new chemical compounds, they are not claimed in the present case, being the subject matter of a parent case, Serial No. 274,488, filed March 1, 1952, of which the present application is a division.

Among the typical ice-color coupling components which may be used in the present invention are compounds such as beta-naphthol; 8- amino-2-naphthol; 8-acetylamino-2-naphthol, benzylnaphthols, pyrazolones, hydroxybenzofluorenones, and the various N-substituted amides such as arylides of 2-hydroxy-3-naphthoic acid, of 2-hydroxy-3-anthroic acid, of methyl and dimethylsalicyclic acids, of hydroxycarbazole carboXylic acids, of hydroxybenzocarbazole carboxylic acids, of hydroxybenzacridone carboxvlic acids, of hydroxydibenzofuran carboxylic acids, of hydroxybenzothiophene carboxylic acids, of acetoacetic acid, of benzoylacetic acid, and the like.

2 This invention is further illustrated by the following examples. Where not otherwise specified, parts are by weight.

Example 1 C sHs-k J-NH- N A mixture of 2.16 parts of 2,4-diphenyl-6- chlorotriazine and 1.93 parts of 2,5-diethoxy-4- aminoacetanilide in 50 parts of 50% dioxanewater containing 8.1 parts of 0.1 N hydrochloric acid is refluxed with stirring. The product shortly begins to separate out from solution, and when the reaction is complete, the mixture is cooled and filtered. The product is washed and dried. The yield is excellent.

Example 2 C 0H5 C 2115 O -NHCOCH1 N N NH:

( H O ONHCoHs The above prepared base is diazotized in the ordinary way with hydrochloric acid and sodium nitrite and used to develop cotton cloth padded with 2-hydroxy-3-naphthoic anilide. Blue dyeings are obtained of extremely greenish 5 shade, and good fastness properties.

Example 4 The procedure of Examples 1 and 2 is followed,

0635 00m OH CONHCQHB OCH;

I claim: 7 1. An azoic coloring having the formula CrsHs OR N N N=NR' CoHsk J-NIEL- N 4 in which R is lower alkyl and R is the residue of an ice-color coupling component.

2. An azoic coloring matter having the formula in which R is lower alkyl.

3. An azoic coloring matter having the formula 0 CH3 4. An azoic coloring matter having the formula 05m 0 02m OH CONHOaHa NAN W8 No references cited. 

1. AN AZOIC COLORING HAVING THE FORMULA 